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A Dame Traveler Insider Guide to Chicago

‘My first day in Chicago, September 4, 1983. I set foot in this city, and just walking down the street, it was like roots, like the motherland. I knew I belonged here.’ – Oprah Winfrey

8 years ago, I took a leap of faith and left everything I’ve ever known in Michigan to start a new life in the city of Chicago. At the age of 20, coming from a strict Middle Eastern family, this was no small feat. I was on my own financially, emotionally and mentally but pushed my way through Loyola University Chicago’s nursing school and successfully graduated and got married. I’ve traveled all over the world but whenever my plane lands in Chicago, my heart flutters and I’m reminded again and again of how much I love this city. It gave me the opportunities and life that I live today and I’ll forever be indebted.

Sadly, I will have to say farewell to this city as I move to NYC to support my husband’s endeavors. This is a bittersweet time for me so I would like to take the opportunity to share some of my favorite spots in this incredibly underrated city and I have teamed up with Choose Chicago to help me do just that!

Stunning architecture, friendly locals, gorgeous Lake Michigan, speakeasys, world class restaurants and more, Chicago truly has something for everyone.

Here’s an insider guide by yours truly:

1.) Take a helicopter ride
Ok ok, I’ve lived in this city and it took me 8 years to get on a helicopter but it was the most EPIC experience I’ve had in Chicago. Chicago Helicopter Experiences Tours took us on a 20 minute ride over the city during twilight hour and it was pretty incredibly to watch the sky turn pink and the sun sink down. Hands down, one of my best Chicago memories to date! Shout out to the staff for having such great energy and for being so helpful and friendly.


2.) Visit during Springtime

Located in the Midwest, Chicago is home to all four gorgeous seasons in all of their glory but Springtime in Chicago is heaven, especially if you are flower obsessed. Michigan Avenue is covered in blankets of tulips and flowering trees tower are all over Grant Park.


View from Cindy's Rooftop located in The Chicago Athletic Association Hotel

View from Cindy’s Rooftop located in The Chicago Athletic Association Hotel

3.) Museum hop and skip long lines with the Chicago CityPASS
Super long line to get up to the Skydeck and 360 Chicago on a sunny Saturday afternoon in Chicago? No problem. With the CityPASS, we zipped past the long lines and went straight up to the roof deck in less than 5 minutes. A HUGE time saver, especially if you have limited time in the city.

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4.) Use your CityPASS to visit The Art Institute of Chicago
A classic and one of my favorites in Chicago, you’ll admire works by Claude Monet, Vincent van Gogh and more.
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Photo op Tip: find this heavenly (and Instagrammable!) staircase in the modern wing.

5.) Be a foodie
Chicago is booming with tons of new restaurants to satisfy your foodie taste buds. One of my favorite off the beaten path spots is Bernie’s Lunch & Supper. We indulged in everything from Pan con Tomate, Lamb Hashwi to Hanger Steak Salad and Croque Madame with their signature (and to die for I might add) Sangria to accompany this epic meal. Bernie’s is chef owned and operated by Chef Zack Sklar and Executive Chef Ryan Sand.

6.) Hang out in cool neighborhoods such as the West Loop
I lived in this neighborhood so I am a bit biased but if you’re artsy and love food, then this is the place to hang out in Chicago. Away from the hoards of tourists and selfie sticks, West Loop is home to famous restaurants such as Girl & the Goat, Au Cheval and more on Randolph Street. You’ll also find cool coffee shops such as The Allis at SohoHouse and Sawada Coffee.

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7.) Splurge on a fancy hotel stay at the iconic Waldorf Astoria Chicago
Located in one of the ritziest neighborhoods in Chicago, the Gold Coast, the Waldorf Astoria will have you feeling like royalty, a little piece of Paris in the Midwest.


All content provided on this blog is for informational purposes only. The owner of this blog makes no representations as to the accuracy or completeness of any information on this site or found by following any link on this site.

I was hosted by Choose Chicago and Waldorf Astoria Hotels. As always, all opinions are my own.



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  • Reply Ray October 20, 2016 at 2:58 am

    You are so right about Chicago being such an under rated city. I’m from Toronto and I find that we have more in common with Chicago than we do with NYC on so many fronts – culture, people, scenery, craft brewery productions, arts & comedy, music, sports culture, etc. Best of luck to your new life in NYC.

  • Reply StephanieRMontgomery September 27, 2017 at 6:18 am

    I really appreciate that you wrote this article and shared some really good information on this specific topic.

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